m-Chloroperbenzoic acid → 3-Chlorobenzoic Acid

Participants

Reaction Steps

To a four-necked 500 ml flask equipped with a mechanical stirrer, thermometer, and condenser, was added -nopol glycidyl ether (48.2 g, 205.4 mmol), and methylene chloride (250 ml). To the solution was added 70% m-chloroperoxybenzoic acid (53 g, 215 mmol) over a period of time of about 2 hours. The reaction temperature was maintained below about 15° C. with an ice/water bath during the addition. After the addition was complete, the reaction mixture was stirred overnight and maintained at a temperature below about 20° C. with an ice water bath. m-Chlorobenzoic acid was formed as a precipitate, and filtered the organic filtrate washed off, twice with 200 ml portions of 10% aq. Na2SO3, twice with 200 ml portions sat. aq. NaHCO3, and twice with 200 ml portions of water. The organic layer was separated, dried over anhydrous MgSO4, and filtered. Solvent was removed under reduced pressure, and the crude product was vacuum distilled. Nopol epoxide glycidyl ether was obtained in a yield of about 46.5 g (91%), with a boiling point of about 110-113° C. at 800 mTorr. 1H NMR (CDCl3) δ 2.8-3.7 (m, 8, OCH, OCH2), 2.0-2.4 (m, 8, CH, CH2), 1.3 (s, 3, CH3) (see FIG. 17), 0.9 (s, 3, CH3); FT-IR 2917, 1470, 1110, 911, 855, 761 cm−1 (see FIG. 18).

Provenance & Evidence